HCID 13252228, compound → HCID 13826492, compound

HRID 1906343Notes

Reaction equation

HRID 1906343 reaction equation
FC(F)(F)C([N:5]([CH2:14][P:15]([NH:22][CH:23]([CH2:25][CH3:26])[CH3:24])([NH:17][CH:18]([CH2:20][CH3:21])[CH3:19])=[S:16])[CH2:6][C:7]([O:9][CH2:10][CH2:11][CH2:12][CH3:13])=[O:8])=O>C(O)C>[CH:23]([NH:22][P:15]([CH2:14][NH:5][CH2:6][C:7]([O:9][CH2:10][CH2:11][CH2:12][CH3:13])=[O:8])([NH:17][CH:18]([CH2:20][CH3:21])[CH3:19])=[S:16])([CH2:25][CH3:26])[CH3:24]

Participants

3

Reactant 1

HCID 13252228HCID 13252228, compound

Product 1

HCID 13826492HCID 13826492, compoundYield 23.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

N-trifluoroacetyl-N-[bis(sec-butylamino)phosphinothioylmethyl]glycine, butyl ester (4 g, 8.9 mm), was dissolved in ethanol (30 ml) and cooled to 0° C. on an ice bath. The solution was stirred and sodium tetrahydrido boron (339 mg, 8.9 mm) was added portionwise over a ten minute period. The solution was allowed to warm to room temperature and stirred for an additional 45 minutes. The solvent was removed by evaporation under vacuum and the residue was washed with water. The water washings were saturated with sodium chloride and the aqueous layer and insoluble residue were simultaneously extracted with ethyl acetate three times. The combined ethyl acetate extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was then chromatographed on silica gel with 5% diethyl ether in dichloromethane (V:V) to yield N-[bis(sec-butylamino)phosphinothioylmethyl]glycine, butyl ester (750 mg), as a yellow oil, ND25 =1.708 and having the following analysis: Calculated: C, 49.93; H, 9.70; N, 11.65. Found: C, 50.11; H, 9.49; N, 11.60.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for an additional 45 minutes
  3. customThe solvent was removed by evaporation under vacuum
  4. washthe residue was washed with water
  5. extractionthe aqueous layer and insoluble residue were simultaneously extracted with ethyl acetate three times
  6. dry with materialThe combined ethyl acetate extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was then chromatographed on silica gel with 5% diethyl ether in dichloromethane (V:V)

Sources & evidence

ORD record
ord-a78ba59cf84341b3b135d8fd9d09467e
Source dataset
uspto-grants-1987_03
Patent number
US04652297

Reaction notes

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